1-Hydroxybenzotriazole → HCID 178425173, compound

HRID 1501251Notes

Reaction equation

HRID 1501251 reaction equation
[O:1]([CH:8]([C:10]1[N:15]=[N:14][C:13]([C:16]([OH:18])=O)=[CH:12][CH:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][C:21]1[C:22]([OH:29])=[N:23][C:24]([CH3:28])=[CH:25][C:26]=1[CH3:27].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[OH:29][C:22]1[C:21]([CH2:20][NH:19][C:16]([C:13]2[N:14]=[N:15][C:10]([CH:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:9])=[CH:11][CH:12]=2)=[O:18])=[C:26]([CH3:27])[CH:25]=[C:24]([CH3:28])[N:23]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581262HCID 89581262, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425173HCID 178425173, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture solution of 6-(1-phenoxyethyl)pyridazine-3-carboxylic acid (60 mg, 0.2 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (37 mg, 0.2 mmol), 1-Hydroxybenzotriazole (30 mg, 0.2 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40 mg, 0.2 mmol) and triethylamine (0.1 mL) in dichloromethane (50 mL) was stirred at room temperature for 18 hours. The mixture solution was diluting with ethyl acetate (50 mL), washed with water (20 mL). The organic layer was concentrated, the residue was purified by column chromatography (silica-gel, dichloromethane/methanol=30:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-(1-phenoxyethyl)pyridazine-3-carboxamide as a yellow solid (60 mg, 64%). LRMS (M+H+) m/z: calcd 379.17. found 379. HPLC Purity (214 nm): 95%. 1H NMR (300 MHz, CDCl3): δ 9.06 (s, 1H), 8.20 (d, J=9 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.15-7.25 (m, 2H), 6.82-6.91 (m, 3H), 5.96 (s, 1H), 5.76-5.78 (m, 1H), 4.63 (d, J=6 Hz, 2H), 2.36 (s, 6H), 1.70 (d, J=6 Hz, 3H).

Workup

  1. washwashed with water (20 mL)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by column chromatography (silica-gel, dichloromethane/methanol=30:1)

Sources & evidence

ORD record
ord-41f6af63750d451fbfd43ac84a05e2d6
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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